It is hard to explain her appeal. She is in many ways inscrutable. Still, I enjoyed her company immensely. "When a person is with Ingrid," says Rosenberg, "you get a different view of the world. She gets you into a certain mind-set and it's just a great place to be." Another friend, Tim Rosta, the executive director of LifeBeat, the music industry's AIDS fund-raising organization, describes Casares as "a Peter Pan." Rosta jokes, "She suffers from attention-deficit disorder, but it's sort of endearing." Says Rosenberg, "She could calm down a little."
At the time of that first meeting, Casares was working as an image consultant for Emilio Estefan (husband of singer Gloria Estefan), who produces Latin artists like Jon Secada and Albita for his and Gloria's record label, Crescent Moon. Casares went to high school with Gloria's younger sister, Becky Fajardo, and has known the family for years. Her first task for Estefan was to make over Secada's deeply unhip, hairy-chested Miami Vice look -- no small feat. That night, in Madonna's kitchen, she didn't waste a minute before pitching her pet project to me -- a losing battle, I thought, as I hated Secada's corny music and image. A week later, back in New York, I was walking to work one morning when I noticed a black limousine slowing next to me. The darkened window glided down and Casares, still pitching Secada, popped her head out. "I'll call you this afternoon," she said, and zipped away. She did call, and by the end of the day I had assigned a piece about Jon Secada. Like so many other schnooks before and after me, I couldn't say no.
Casares occupies an odd and singular place in America's celebrity culture: Best Friend to Very Famous Sexually Ambiguous Women. Strangely enough, there is a precedent -- a Cuban woman named Mercedes de Acosta who was the nonfamous best friend to both Greta Garbo and Marlene Dietrich, for all intents and purposes the cool bisexual chicks of their day. In Antoni Gronowicz's book Garbo: Her Story, the actress reminisced: "My most original friendship was the one with Mercedes de Acosta, a woman with a small figure, a sharp nose, and a great appetite for arts and for life." Physical parallels aside, the two women share an old-fashioned social role usually reserved for gay men by Upper East Side ladies: the perfect accessory, or "extra man." Ingrid Casares is a lesbian walker, a female Truman Capote minus the writing chops.
"She became the ideal escort, the total confidante, pal, and glamorous companion for Madonna, or Sandra, or Ingrid Sischy editor of Interview," says Sarah Pettit, the former editor of Out magazine, who has traveled a bit herself in the ever-more-crowded fabulous-lesbian orbit. "In a funny way, she has played this dashing Holly Golightly girl that a lot of lesbians would hate to admit that they want to be but actually do."
When I asked Casares to define her sexuality, she said, "I don't define myself in any way. I fall in love with someone's soul -- I'm not gender-specific. I've fallen in love with men and women."
"But you've become a famous lesbian," I said. "Yeah, I guess so," she said with a shrug, "but that's because I've had high-profile female affairs."
While Casares is not a household lesbian name in America like Ellen DeGeneres or k. d. lang, in queer circles she definitely stands for something, whether she likes it or not. There's the simple fact that she's attractive to women. "There was a period where it was all about Ingrid, the girl-toy," says Pettit. " 'Who is she sleeping with?' I was actually very embarrassed to find myself the other day discussing her with another lesbian, and I said, 'You think Ingrid's cute? I would never have expected that of you.' Ingrid has that versatile mixture of being very impish and pixie but also being sufficiently butch. You sort of feel like she's wearing the pants when she's with Madonna."
Additionally, she has confounded people by being so publicly associated with fashion and beauty, things not considered serious enough for a lesbian. "What she really is," says Pettit, "is the worst vice that you could be as a lesbian, which is somebody who is extremely social-climby, fairly concerned with artifice, and totally unashamed about it. In earlier times, that was considered a total lesbian no-no. But obviously, she's nobody's fool, and she sort of said, 'Screw it. I am this person.' She became her own inventor in a way, and if she had to go before a panel of lesbian experts, they would have turned her down. You have to be doing something for the cause."
Other lesbians have a much less generous take on Casares. "She's a loathsome, pretentious, shallow social butterfly who's been skating along on her family's money," says Camille Paglia. "She's turned herself into Madonna's flunky and yes-girl, and I think Madonna's dependence on Ingrid Casares is a self-stunting sickness. Madonna should go to the Betty Ford clinic to break her addiction and detox from Ingrid Casares."
Ingrid Casares was born in 1964 in Miami in Little Havana, just a couple of years after her parents, Nancy and Raul, left Cuba during the revolution. She was raised in tony Coral Gables, a wealthy Miami suburb where Wasps and rich Cubans play golf together. Theirs is the classic Cuban-exile story: lost everything, worked hard, became wealthy Republicans, sent kids to private Catholic school. Casares has a younger sister, Lourdes (!), who is now a psychologist, and an older one, Nancy, who has two kids and works in her father's business, which Casares describes as "aluminum, windows, and sliding glass doors for high-rise construction." Their mother is a housewife, "very beautiful, very young-looking," says Casares.
She attended Our Lady of Lourdes (!!) Academy, a strict private girls' school, where she was, all at once, bad girl, class clown, and star athlete. (Casares was an all-county basketball player with the highest scoring average in Dade County.) "Boys, parties, and sports," says Casares, listing, in order of importance, her main activities in high school. "At some point, sports weren't important to me anymore. I should probably have kept going on that road. I was very good. I was the leader in a lot of ways, and I hung out with all the popular kids and the athlete boys and the cheerleader girls. It was the whole Cuban, decadent, A-crowd thing. But I always felt a bit different. I was a lot more liberal than most. There's a certain way that Catholic Cuban girls are raised -- very conservative -- that I didn't necessarily adhere to. It was very confining, and it wasn't me."
"She was always in trouble," says Becky Fajardo, Gloria Estefan's sister, who has known Casares since she was 14. "In her senior year, in order for her to graduate, her mother had to sit in every class with her." Casares is allergic to cats, says Fajardo, "and she used to rub cats on her face in the morning so that she wouldn't have to go to school. She was a bit of a freak." When I ask Fajardo if any of her old friends are surprised by her fame, she says, "Not at all. You just knew that Ingrid was going to be infamous, because I think she's infamous more than famous. I can't get over every time I see her with the biggest celebrities in the world in the oddest places in the world. And this is a person who's never really done anything." Fajardo, who says they're still good friends, can't hide her hostility: "She kind of whirlwinds into your life and whirlwinds out. And whenever she needs a little sanity, she calls, and that's it."